Novel antimicrobial compositions and articles made therefrom

Abstract

Antimicrobial compositions and articles, and methods for preparing the antimicrobial compositions, are disclosed. Methods of using the antimicrobial compositions and articles to prevent biofilm formation or growth, disrupt biofilms, reduce microbial populations, and treat infections are also disclosed.

Description

[Background technology]

[0001] There is growing interest in our ability to prevent and treat microbial infections. Over 2% of the U.S. population suffers from non-healing (i.e., chronic) wounds, which cost the U.S. healthcare system over $20 billion annually to manage. Wound management often involves the use of adhesive dressings and antimicrobial compositions. In some cases, the antimicrobial composition is used as a topical cream or ointment, and in other cases, the antimicrobial composition is incorporated into the adhesive itself. In either case, maintaining adhesive properties in the presence of the antimicrobial composition is difficult, which leads to unintended microbial exposure and frequent dressing changes.

[0002] Despite advances made in infection control practices, surgical site infections (SSIs) remain a substantial cause of morbidity, prolonged hospital stays, and mortality. In fact, SSIs are associated with 3% of mortality rates, and 75% of SSI-related deaths are directly attributable to SSIs. Surgeons rely on surgical drapes with iodine-impregnated adhesives to reduce contact with pathogenic microorganisms. However, the antimicrobial properties are typically only effective as long as the drape is securely attached to the skin.

[0003] Developing new antimicrobial adhesives with better adhesive and antimicrobial properties will help reduce infections. What is needed are pressure-sensitive adhesives that can carry and deliver different types of antimicrobial agents. Summary of the Invention

[0004] In one embodiment, an antimicrobial composition is described. The antimicrobial composition may include a polymerizable mixture including at least one high Tg monomer, and optionally a homopolymer thereof, wherein the homopolymer has a Tg of about 40° C. to about 250° C., and at least one low Tg monomer, and optionally a homopolymer thereof, wherein the homopolymer has a Tg of about −70° C. to about 30° C.; an organic acid chelating agent, a salt thereof, or a combination thereof, having a molecular weight of less than about 400 g / mol; and a water-soluble plasticizer capable of solubilizing the organic acid chelating agent or its salt in an amount of at least about 100 g of chelating agent per liter of plasticizer at a temperature of about 20° C. to about 23° C. After polymerization, the polymerizable mixture forms a water-insoluble polymer composition comprising a copolymer derived from the at least one high Tg monomer and the at least one low Tg monomer.

[0005] In one embodiment, an antimicrobial composition is described. The antimicrobial composition may include a water-insoluble polymer composition including a copolymer derived from a polymerizable mixture including at least one high Tg monomer and optionally its homopolymer, wherein the homopolymer has a Tg of about 40°C to about 250°C, and at least one low Tg monomer and optionally its homopolymer, wherein the homopolymer has a Tg of about -70°C to about 30°C; an organic acid chelating agent having a molecular weight of less than about 400 g / mol, a salt thereof, or a combination thereof; and a water-soluble plasticizer capable of solubilizing the organic acid chelating agent or its salt in an amount of at least about 100 g of chelating agent per liter of plasticizer at a temperature of about 20°C to about 23°C. The antimicrobial composition may be a pressure-sensitive adhesive.

[0006] In one embodiment, an antimicrobial article is described. The antimicrobial article may comprise a substrate having a first surface and a second surface opposite the first surface, and an antimicrobial composition described herein disposed on the first surface.

[0007] In one embodiment, a method for preparing an antimicrobial pressure-sensitive adhesive is described. The method may include providing an antimicrobial composition described herein and irradiating the antimicrobial composition and a photoinitiator with electromagnetic radiation at a wavelength of from about 280 nm to about 500 nm for a period of time to at least partially cure the antimicrobial composition.

[0008] In one embodiment, a method for preparing an antimicrobial pressure-sensitive adhesive is described. The method may include providing the antimicrobial composition described herein and a photoinitiator. The method may include providing the antimicrobial composition and the photoinitiator with a photoirradiation source at about 0.01 to about 20 milliwatts per square centimeter (mW / cm). 2 ), wherein the irradiation is effective to polymerize about 5% to about 70% by weight of the monomers to provide the polymer composition. The method may include irradiating the polymer composition with electromagnetic radiation having a wavelength of about 280 to 500 nanometers at an average light intensity of about 20 mW / cm 2 The method may include irradiating the substrate with electromagnetic radiation having a wavelength of about 280-500 nm at an average light intensity of greater than 1000 nm to provide an antimicrobial pressure sensitive adhesive.

[0009] In one embodiment, a method for preventing or disrupting a biofilm on a surface is described. The method may include providing an antimicrobial article as described herein and contacting the antimicrobial article with the surface for a period of time, wherein the contact is effective to prevent the formation or growth of a biofilm or to disrupt an existing biofilm on the surface.

[0010] In one embodiment, a method for reducing the number of microorganisms on a surface is described. The method may include providing an antimicrobial article as described herein and contacting the antimicrobial article with the surface for a period of time, wherein the contacting is effective to reduce the number of microorganisms in the area of ​​the surface contacted by the antimicrobial article. In one embodiment, a method for reducing the number of microorganisms on a surface is described. The method may include providing an antimicrobial article as described herein and contacting the antimicrobial article with the surface for a period of time, wherein the contacting is effective to reduce the number of microorganisms in the area of ​​the surface contacted by the antimicrobial article.

[0011] In one embodiment, a method for treating or preventing an infection is described. The method may include providing an antimicrobial article described herein and contacting the antimicrobial article with a surface in need of disinfection. The contacting may be effective in reducing one or more symptoms of the infection. The contacting may be effective in preventing the onset of the infection.

[0012] In one embodiment, a kit is described. The kit may include any of the antimicrobial compositions described herein and a set of instructions directing a user to perform the steps recited in any of the methods described herein. DETAILED DESCRIPTION OF THE INVENTION

[0013] Efforts to develop alternative antimicrobial-impregnated adhesives have faced various challenges. For example, antimicrobial agents tend to precipitate from the adhesive composition, thereby immobilizing the antimicrobial agent and making it unavailable for migration to the surface. Furthermore, blending the antimicrobial agent with the adhesive tends to reduce the effectiveness of the antimicrobial activity. Similarly, blending the antimicrobial agent with the adhesive tends to reduce the adhesive's bond strength, leading to premature failure of the adhesive. This premature adhesive failure, when referring to surgical drapes, is referred to as "drape drift." When surgical drapes move or "drift," patients are exposed to increased microorganisms, making them more vulnerable to infection.

[0014] Current antimicrobial adhesive technology is limited to a small number of antimicrobial agents, primarily for the reasons discussed above. The present disclosure relates to antimicrobial compositions suitable for incorporation into pressure-sensitive adhesives without sacrificing either antimicrobial activity or adhesive properties. The antimicrobial compositions described herein utilize an organic acid chelating agent with antimicrobial properties and a plasticizer that aids in the incorporation of the organic acid chelating agent into the pressure-sensitive adhesive. Organic acid chelating agents for use in antimicrobial adhesives are highly beneficial because they are much less cytotoxic than antimicrobial agents currently formulated in adhesives.

[0015] As used herein, "about" means plus or minus ten percent of a given value. For example, about ten means nine to eleven.

[0016] As used herein, "alkyl" refers to a straight or branched chain hydrocarbon group. 1~6 "Alkyl" refers to the number of carbon atoms in the hydrocarbon group. For example, C 1~6 means 1 to 6 carbons, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, pentyl, hexyl, and the like.

[0017] As used herein, "copolymer" refers to a chemical compound having two or more chemically different monomers polymerized together.

[0018] As used herein, "cycloalkyl" refers to a cyclic hydrocarbon group. Cyclic hydrocarbon groups are intended to include monocyclic, fused bicyclic, bridged bicyclic and spiro bicyclic groups, fused tricyclic, bridged tricyclic and spiro tricyclic groups, and the like. 5~7 "Cycloalkyl" refers to the number of carbon atoms in the cyclic hydrocarbon group, e.g., cyclopentyl, cyclohexyl, cycloheptyl, norbornyl, and the like.

[0019] As used herein, "essentially free" means present in an amount of less than 0.1% by weight based on the weight of the composition being described.

[0020] As used herein, "derived" means that component X can be prepared from component Y, for example, water-insoluble polymer X can be prepared from monomer Y.

[0021] As used herein, the "glass transition temperature" or "Tg" of any homopolymer described herein is used to characterize the respective monomer. Glass transition temperatures are measured by differential scanning calorimetry (DSC).

[0022] As used herein, "halogen" or "halogenated" refers to a group having one or more halogen atoms, i.e., I, Br, Cl, or F.

[0023] As used herein, "homopolymer" refers to a chemical compound having only one polymerized monomer. The molecular weight of the homopolymer present in the compositions described herein is not intended to be limited by the glass transition temperature of a given homopolymer molecular weight. In other words, the composition containing a homopolymer is not limited to the exact molecular weight of the homopolymer characterized by the glass transition temperature described.

[0024] As used herein, "hydroxyl" or "hydroxylated" refers to a group having one or more --OH groups.

[0025] As used herein, "monomer" refers to a chemical compound having at least one unsaturated polymerizable functional group, such as an alkenyl group (i.e., -CR=CR-, where R is optional), an alkynyl group (i.e., -C≡C-), etc. A monomer having an alkenyl or alkynyl group is referred to herein as an unsaturated monomer.

[0026] As used herein, "organic chelator acid" refers to an aliphatic or aromatic compound having at least two acid groups, i.e., -COH, -P(O)(OH), -S(O)OH, -S(O)OH, or salts thereof.

[0027] As used herein, "optionally substituted" refers to a chemical entity that may or may not be substituted with one or more described chemical moieties. For example, "C optionally substituted with one or more hydroxyl" refers to a 1~6 "Alkyl group" refers to an unsubstituted C 1~6 C substituted with alkyl group or one or more -OH1~6 Alkyl groups such as 2-hydroxybutyl are intended to be included.

[0028] As used herein, "polymerization" refers to a chemical process in which monomers chemically react to form polymer chains or networks. Polymerizations described herein may be step-growth or chain-growth. Polymerizations may be radical-initiated, acid- or base-initiated, photoinitiated, or organometallic-catalyzed.

[0029] As used herein, "pressure sensitive adhesive" refers to a non-reactive, self-sticking adhesive that forms a bond when pressure is applied. No solvents, water, or heat are required to activate a pressure sensitive adhesive.

[0030] When referring to "solubility," it should be understood that the solubility of component A in component B refers to the state in which only components A and B are present, e.g., without added salts, compounds, etc. Furthermore, any solubility values ​​provided herein relate to a temperature range of about 20°C to about 23°C at atmospheric pressure (i.e., 760 mm / Hg). As used herein, "solubilized" or "solubilize" means freely soluble, i.e., requiring 1 to 10 parts by weight of solvent to completely dissolve 1 part by weight of solute. Freely soluble and completely dissolved are synonymous with homogeneous.

[0031] As used herein, "preventing" or "prevent" refers to slowing or stopping the accumulation or growth of microorganisms.

[0032] As used herein, "treating" or "treatment" refers to reducing the number of microorganisms present on a surface, which reduction in the number of microorganisms results in amelioration of symptoms associated with the presence of the microorganisms.

[0033] As used herein, "water-insoluble" is used to describe a compound or complex that has an octane:water partition coefficient (Log Kow) greater than zero (0). A water-insoluble material, as used herein, has a water solubility of less than 15% w / w by weight of water.

[0034] As used herein, "water soluble" is used to describe a compound or complex that has an octane:water partition coefficient (Log Kow) of less than zero (0). A water soluble material, as used herein, has a water solubility of greater than 15% w / w based on the weight of the water.

[0035] Antibacterial composition - uncured In many embodiments, antimicrobial compositions are described. The antimicrobial compositions may include a polymerizable mixture including at least one high Tg monomer, and optionally a homopolymer thereof, wherein the homopolymer has a Tg of about 40° C. to about 250° C., and at least one low Tg monomer, and optionally a homopolymer thereof, wherein the homopolymer has a Tg of about −70° C. to about 30° C.; an organic acid chelating agent, a salt thereof, or a combination thereof, having a molecular weight of less than about 400 g / mol; and a water-soluble plasticizer capable of solubilizing the organic acid chelating agent or its salt in an amount of at least about 100 g of chelating agent per liter of plasticizer at a temperature of about 20° C. to about 23° C. After polymerization, the polymerizable mixture forms a water-insoluble polymer composition comprising a copolymer derived from the at least one high Tg monomer and the at least one low Tg monomer.

[0036] In some embodiments, the antimicrobial composition may include one or more high Tg monomers. For example, the antimicrobial composition may include 1 to 5 high Tg monomers. In some embodiments, the antimicrobial composition may include one or more low Tg monomers. For example, the antimicrobial composition may include 1 to 5 low Tg monomers. In some embodiments, the antimicrobial composition may include one high Tg monomer and one low Tg monomer. In other embodiments, the antimicrobial composition may include one high Tg monomer and two to three low Tg monomers. The number and types of high Tg monomers and low Tg monomers may be selected based on common knowledge in the art to achieve desired properties.

[0037] In some embodiments, the antimicrobial composition may include at least one high Tg monomer present in an amount of about 1 part by weight to about 50 parts by weight of the polymerizable mixture. For example, the at least one high Tg monomer may be present in about 1, 5, 10, 15, 20, 25, 30, 35, 40, 45, or 50 parts by weight of the polymerizable mixture, or a value within a range between any of the foregoing values, such as about 15 to about 30 parts by weight, about 40 to about 50 parts by weight, etc.

[0038] In some embodiments, the antimicrobial composition may include at least one low Tg monomer present in an amount of about 50 parts by weight to about 99 parts by weight of the polymerizable mixture. For example, the at least one low Tg monomer may be present in about 50, 55, 60, 65, 70, 75, 80, 85, 90, 95, or 99 parts by weight of the polymerizable mixture, or a value within a range between any of the foregoing values, such as about 60 to about 75 parts by weight, about 50 to about 80 parts by weight, etc.

[0039] In some embodiments, the polymerizable mixture may further comprise at least one intermediate Tg monomer, and optionally a homopolymer thereof, the homopolymer having a Tg of about −20° C. to about 70° C. In some embodiments, the antimicrobial composition may comprise at least one intermediate Tg monomer present in an amount of about 5 parts by weight to about 50 parts by weight of the polymerizable mixture. For example, the at least one intermediate Tg monomer may be present in about 5, 10, 15, 20, 25, 30, 35, 40, 45, or 50 parts by weight of the polymerizable mixture, or a value within a range between any of the foregoing values, e.g., about 5 to about 10 parts by weight, about 20 to 30 parts by weight, etc.

[0040] In some embodiments, the antimicrobial composition may include an organic acid chelating agent, a salt thereof, or a combination thereof present in an amount of about 1% to about 25% by weight based on the weight of the antimicrobial composition. For example, the organic acid chelating agent and / or salt thereof may be present in an amount of about 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 15, 20, or 25% by weight based on the weight of the antimicrobial composition, or a value within a range between any of the foregoing values, such as about 5 to about 10% by weight, about 4 to about 20% by weight, etc.

[0041] In some embodiments, the antimicrobial composition may further comprise water in an amount less than about 1 wt. % based on the weight of the antimicrobial composition. For example, the antimicrobial composition may comprise water present in an amount of about 1, 0.9, 0.8, 0.7, 0.6, 0.5, 0.4, 0.3, 0.2, 0.1, 0.05, 0.02, 0.01 wt. % based on the weight of the antimicrobial composition, or within a range between any of the foregoing values, e.g., about 0.02 to about 0.1 wt. %, about 0.05 to about 0.3 wt. %, etc. In some embodiments, the antimicrobial composition may comprise less than about 1 wt. % water based on the weight of the antimicrobial composition.

[0042] In some embodiments, the antimicrobial composition may include a water-soluble plasticizer present in an amount of about 3% to about 25% by weight, based on the weight of the antimicrobial composition. For example, the water-soluble plasticizer may be present in an amount of about 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 20, or 25% by weight, or a range between any of the foregoing values, such as about 10 to about 15% by weight, about 8 to about 25% by weight, etc. In some embodiments, the antimicrobial composition may include the water-soluble plasticizer and organic acid chelating agent present in amounts that balance antimicrobial and adhesive properties.

[0043] In some embodiments, the antimicrobial composition may further comprise one or more additional antimicrobial agents, such as an antimicrobial quaternary amine compound (e.g., benzalkonium chloride) or a salt thereof, a cationic surfactant (e.g., cetylpyridinium chloride, cetyltrimethylammonium bromide, etc.), a polycationic compound such as octenidine or a salt thereof, a biguanide compound (e.g., chlorhexidine, polyhexamethylene biguanide (PHMB) or a salt thereof, a (C6-C12)1,2-organic diol (e.g., 1,2-octanediol), an antimicrobial fatty acid monoester compound, and combinations of any two or more of the foregoing antimicrobial components. Preferred additional antimicrobial agents include antimicrobial lipids, phenolic preservatives, cationic preservatives, iodine and / or iodophors, peroxide preservatives, antimicrobial natural oils, C6-C12 alkanediols, silver, silver salts and complexes, silver oxide, copper, copper salts, or combinations thereof.

[0044] In some embodiments, the antimicrobial composition excludes antimicrobial compounds other than organic acid chelating agents.

[0045] In some embodiments, the polymerizable mixture may further include a photoinitiator, which may be present at about 0.01% to about 1% by weight of the antimicrobial composition.

[0046] In some embodiments, the antimicrobial composition comprises one or more C 6~12Alkyl diol synergists may also be included, such as 1,2-alkanediols, ethylhexylglycerin, fatty acid monoesters, alcohols, and the like.

[0047] In some embodiments, the antimicrobial composition may be characterized by a pH of about 3 to about 10. In some embodiments, the antimicrobial composition may be characterized by a pH of 3, 4, 5, 6, 7, 8, 9, or 10, or a value within a range between any of the foregoing values, such as about 4 to about 5, about 6 to about 8, etc. In other embodiments, the pH may be about 3 to about 12. Compositions with higher pHs can be achieved using added bases, such as NaOH, KH2PO4, Na2CO3, NH3, NaClO, Mg(OH)2, NaHCO3, etc.

[0048] In some embodiments, the antimicrobial composition may include one or more surfactants. In other embodiments, the antimicrobial composition may be essentially free of surfactants. In other embodiments, the antimicrobial composition may be free of surfactants, i.e., 0% by weight surfactant.

[0049] In some embodiments, the antimicrobial composition consists essentially of at least one high Tg monomer, at least one low Tg monomer, an organic acid chelating agent, and a water-soluble plasticizer.

[0050] In some embodiments, the antimicrobial composition consists essentially of at least one high Tg monomer, at least one low Tg monomer, at least one medium Tg monomer, an organic acid chelating agent, and a water-soluble plasticizer.

[0051] polymerizable mixture High Tg Monomer In some embodiments, any polymerizable mixture described herein may include at least one high Tg monomer having a Tg of about 40° C. to about 250° C. For example, the at least one high Tg monomer may have a Tg of about 40, 50, 60, 70, 80, 90, 100, 110, 120, 130, 140, 150, 160, 170, 180, 190, 200, 210, 220, 230, 240, or 250° C., or a Tg value within any of the foregoing ranges, such as about 70 to about 100° C., about 80 to about 250° C., about 100 to about 230° C., etc.

[0052] In some embodiments, the polymerizable mixture may include two or more high Tg monomers. For example, the monomer mixture may include one to five high Tg monomers described herein. In some embodiments, the polymerizable mixture may include one high Tg monomer described herein. In other embodiments, the polymerizable mixture may include two high Tg monomers described herein.

[0053] In some embodiments, the at least one high Tg monomer has formula (I): [ka] [In the formula, X is -C(O)OR 4a , -C(O)N(R 5a )(R 5a ), -CN, -N(R 5a )-C(O)-R 6a is selected from R 1a C may be independently substituted with -H, one or more -OH 1~6 Alkyl, -(CH2) n -C(O)-R 7a is selected from R 2a C may be independently substituted with -H, one or more -OH 1~6 alkyl; or R 2a and R 4a , or R 2aand R 5a together with the atoms to which they are attached form a 5- or 6-membered heterocyclic ring, R 3a C, which may be independently substituted with -H, -OH, or one or more -OH 1~6 alkyl, R 4a -H, C 1~6 Alkyl or one or more C 1~4 C optionally substituted with alkyl 4~8 is cycloalkyl, Each R 5a C may be independently substituted with -H or one or more -OH 1~6 is alkyl, R 6a is -H or C 1~6 alkyl, or R 5a and R 6a together with the atoms to which they are attached form a 4- to 7-membered heterocyclic ring, R 7a -OR 8a or -N(R 8a )(R 8a ) or R 7a and R 4a , or R 7a and R 5a together with the atoms to which they are attached form a 5- or 6-membered heterocyclic ring, Each R 8 are independently -H and C 1~6 alkyl, and n is an integer selected from 1 to 6.

[0054] In some embodiments, the at least one high Tg monomer is selected from the group consisting of acrylic acid, (alkyl)acrylic acid, (hydroxyalkyl)acrylic acid, alkyl acrylate, alkyl(alkyl)acrylate, alkyl(hydroxyalkyl)acrylate, hydroxy(alkyl)acrylate, hydroxy(alkyl)(alkyl)acrylate, hydroxy(alkyl)(hydroxyalkyl)acrylate, (hydroxyalkyl)acrylate, (alkyl)acrylamide, (hydroxyalkyl)acrylamide, α,β-unsaturated diacid, α,β-unsaturated diester, α,β-unsaturated cyclic anhydride, N-alkyl(alkyl)acrylamide, N-alkyl(

[0049] The alkyl hydroxyalkyl (hydroxyalkyl) acrylamide may be selected from N-hydroxyalkyl (alkyl) acrylamide, N-hydroxyalkyl (hydroxyalkyl) acrylamide, N,N-alkyl (alkyl) acrylamide, N,N-hydroxyalkyl (alkyl) acrylamide, N-alkyl,N-hydroxyalkyl (alkyl) acrylamide, N,N-alkyl (hydroxyalkyl) acrylamide, N,N-hydroxyalkyl (hydroxyalkyl) acrylamide, N-alkyl,N-hydroxyalkyl (hydroxyalkyl) acrylamide, (alkyl) acrylonitrile, N-vinyl lactam, and any combination thereof.

[0055] In some embodiments, the at least one high Tg monomer may be selected from acrylic acid, methacrylic acid, acrylamide, acrylonitrile, methacrylonitrile, 2-hydroxyethyl acrylate, N-methylacrylamide, N-vinylpyrrolidone, N-vinylcaprolactam, maleic anhydride, isobornyl acrylate, itaconic acid, and any combination thereof.

[0056] In some embodiments, the at least one high Tg monomer may be acrylic acid.

[0057] Low Tg Monomer In some embodiments, any polymerizable mixture described herein may include at least one low Tg monomer having a Tg of about −60° C. to about 30° C. For example, the at least one low Tg monomer may have a low Tg of about −60, −70, −60, −50, −40, −30, −20, −10, 0, 10, 20, or 30° C., or within any of the aforementioned ranges, e.g., about −70 to about 0° C., about −50 to 10° C.

[0058] In some embodiments, the polymerizable mixture may include two or more low Tg monomers. For example, the polymerizable mixture may include 1 to 5 low Tg monomers described herein. In some embodiments, the polymerizable mixture includes one low Tg monomer described herein. In other embodiments, the polymerizable mixture includes two low Tg monomers described herein.

[0059] In some embodiments, the at least one low Tg monomer has formula (II): [ka] [In the formula, Y is -C(O)OR 4b or -OC(O)-(C 1~6 alkyl), R 1b are independently -H or C 1~18 alkyl, R 2b are independently -H or C 1~18 alkyl, R 3b are independently -H or C 1~18 alkyl, R 4b C, which may be independently substituted with -H or one or more of -OH and -CN 1~18 alkyl, R 1 , R 2 , R 3 , or R 4 At least one of the 4~18The compound may be selected from compounds represented by the formula:

[0060] In some embodiments, the at least one low Tg monomer is C 4~18 alkyl acrylates.

[0061] In some embodiments, the at least one low Tg monomer may be selected from isooctyl acrylate, isononyl acrylate, isoamyl acrylate, isodecyl acrylate, 2-ethylhexyl acrylate, n-butyl acrylate, sec-butyl acrylate, tert-butyl acrylate, butyl methacrylate, vinyl acetate, lauryl acrylate, octadecyl acrylate, 4-hydroxybutyl acrylate, and any combination thereof, and the like.

[0062] In some embodiments, the at least one low Tg monomer may be isooctyl acrylate.

[0063] Mid-Tg monomer In some embodiments, any monomer mixture described herein may further include at least one mid-Tg monomer having a Tg of about −20° C. to about 70° C. For example, the at least one mid-Tg monomer can have a mid-Tg of about −20, −10, 0, 10, 20, 30, 40, 50, 60, or 70° C., or a Tg value within any of the foregoing ranges, such as about 20 to about 60° C., about −10 to 30° C., etc.

[0064] In some embodiments, the polymerizable mixture may include two or more mid-Tg monomers described herein. For example, the polymerizable mixture may include one to five mid-Tg monomers described herein. In some embodiments, the polymerizable mixture may include one mid-Tg monomer described herein. In other embodiments, the polymerizable mixture may include two mid-Tg monomers described herein.

[0065] In some embodiments, the at least one mid-Tg monomer may be hydroxyethyl acrylate.

[0066] Monomer Combinations In some embodiments, the polymerizable mixture can include at least one high Tg monomer and at least one low Tg monomer in a weight ratio of about 1:99 to about 20:80. For example, the weight ratio of the at least one high Tg monomer to the at least one low Tg monomer can be 1:99, 2:98, 3:97, 4:96, 5:95, 6:94, 7:93, 8:92, 9:91, 10:90, 11:89, 12:88, 13:87, 14:86, 15:85, 16:84, 17:83, 18:82, 19:81, or 20:80, or a ratio within any of the foregoing values, such as about 1:99 to about 5:95, about 10:90 to about 15:85, etc.

[0067] In some embodiments, the monomer mixture may include two low Tg monomers and one high Tg monomer.

[0068] In some embodiments, the polymerizable mixture may further comprise at least one mid-Tg monomer present in a weight ratio relative to the at least one high Tg monomer of about 30:70 to 70:30. For example, the weight ratio of mid- to high Tg monomer to at least one high Tg monomer may be 30:70, 35:65, 40:60, 45:55, 50:50, 55:45, 60:40, 65:35, or 70:30, or any ratio within any of the foregoing ranges, such as 45:55 to about 65:35, about 50:50 to about 60:40, etc.

[0069] In some embodiments, the polymerizable mixture may further comprise at least one intermediate Tg monomer present relative to the at least one low Tg monomer in a weight ratio of about 1:99 to about 20:80. For example, the weight ratio of the at least one intermediate Tg monomer to the at least one low Tg monomer may be 1:99, 2:98, 3:97, 4:96, 5:95, 6:94, 7:93, 8:92, 9:91, 10:90, 11:89, 12:88, 13:87, 14:86, 15:85, 16:84, 17:83, 18:82, 19:81, or 20:80, or a range therebetween, such as, for example, about 1:99 to about 5:95, about 10:90 to about 15:85, etc.

[0070] In some embodiments, the polymerizable mixture may further include at least one mid-Tg monomer present in a weight ratio of about 5:1:95 to about 19:1:80 relative to the at least one high Tg monomer and at least one low Tg monomer. For example, the weight ratio of the mid-Tg monomer, high Tg monomer, and low Tg monomer may be 5:1:94, 6:1:93, 7:1:92, 8:1:91, 9:1:90, 10:1:89, 15:1:84, or 19:1:80, or any ratio within any of the foregoing ranges, such as, for example, about 5:1:94 to about 10:1:89.

[0071] In some embodiments, the polymerizable mixture may include acrylic acid and isooctyl acrylate. The acrylic acid and isooctyl acrylate may be present in any of the amounts or ratios described.

[0072] In some embodiments, the polymerizable mixture may include acrylic acid, isooctyl acrylate, and hydroxyethyl acrylate. The acrylic acid, isooctyl acrylate, and hydroxyethyl acrylate may be present in any of the amounts or ratios described above.

[0073] In some embodiments, the polymerizable mixture may include isooctyl acrylate, 4-hydroxybutyl acrylate, acrylic acid, and hydroxyethyl acrylate in any of the amounts or ratios described above.

[0074] Organic Acid Chelating Agents In many embodiments, the organic acid chelating agents or salts thereof described herein have antibacterial properties. Without being bound by theory, it is believed that the organic acid chelating agents or salts thereof can chelate metal cations lodged within the phospholipid membranes of various organisms. Furthermore, it is believed that the sequestration of metal cations leads to cell lysis. In some embodiments, the sequestered metal cation is a divalent metal cation. Examples of divalent metal cations include Zn 2+ , Ca 2+ , Mg 2+ , Fe 2+ Examples include:

[0075] The organic chelator acid may further comprise a heteroatom selected from amine (-NR-), ether (-O-), alcohol (-OH), ester (-CO-), acid (-COH), amide (-C(O)NR-), amidine (-C(NR)NR-), oxime (-C(NOR)-), urea (-NRC(O)NR-), carbamate (-NRC(O)O- or -OC(O)NR-), guanidine (-NRC(NR)NR-), thiol ether (-S-), thiol (-SH), sulfoxide (-C(O)S- or -SC(O)-), sulfone (-S(O)-), and the like.

[0076] In some embodiments, the organic acid chelators described herein may be aliphatic. In some embodiments, the organic acid chelators may be aliphatic having 10 or fewer carbons. In some embodiments, the organic acid chelators may be aliphatic having 8 or fewer carbons. In some embodiments, the organic acid chelators may be aliphatic having 6 or fewer carbons.

[0077] In other embodiments, the organic acid chelators described herein may be aromatic, i.e., may have an aromatic group. In some embodiments, the organic acid chelator having an aromatic group may be an aryl alkyl organic acid chelator. In some embodiments, the organic acid chelator may be aromatic having 10 or fewer carbons. In some embodiments, the organic acid chelator may be aromatic having 8 or fewer carbons. In some embodiments, the organic acid chelator may be aromatic having 6 or fewer carbons.

[0078] In some embodiments, the organic acid chelators described herein contain one or more organic acid groups, such as, for example, -C(=O)OH, -P(=O)(OH), -S(=O)OH, -S(=O)OH, combinations thereof, or salts thereof, such as, for example, -C(=O)OM. + , -P(=O)(OH)OM + , -P(=O)O-22(M + ), -S(O)2O-M + , -S(O)O-M+, combinations thereof, etc. In some embodiments, M + Li + , Na + , K. + , Cs + , Ag + It may be selected from the following.

[0079] In some embodiments, the organic acid chelators described herein contain at least two organic acid groups, such as, for example, —C(O)OH, —P(O)(OH), —S(O)OH, —S(O)OH, combinations thereof, or salts thereof, such as, for example, —C(═O)OM. + , -P(=O)(OH)OM + , -P(=O)(O-)22(M + ), -S(O)2O-M + , -S(O)OM + , combinations thereof, etc. In some embodiments, M + Li + , Na + , K. +, Cs + , Ag + It may be selected from the following.

[0080] In some embodiments, the organic acid chelators described herein contain at least three organic acid groups, such as, for example, —C(O)OH, —P(O)(OH), —S(O)OH, —S(O)OH, combinations thereof, or salts thereof, such as, for example, —C(═O)OM. + , -P(=O)(OH)OM + , -P(=O)(O-)22(M + ), -S(O)2O-M + , -S(O)OM + , combinations thereof, etc. In some embodiments, M + Li + , Na + , K. + , Cs + , Ag + It may be selected from the following.

[0081] In some embodiments, the organic acid chelator may have only -C(O)OH acid groups or salts thereof.

[0082] In some embodiments, the organic acid chelator comprises one or more organic acid groups or salts thereof, as described above, and one or more electron donating groups, such as —OH, —O(C 1~6 alkyl), ═O, ═NH, ═N(C 1~6 alkyl), -NH3, -NH2(C 1~6 alkyl), -NH(C 1~6 alkyl)2, and -N(C 1~6 alkyl)3 (wherein C 1~6 wherein any of the groups may be substituted with —C(O)OH.

[0083] In some embodiments, the organic acid chelator comprises two or more organic acid groups or salts thereof as described above and one or more electron donating groups, such as —OH, —O(C 1~6 alkyl), ═O, ═NH, ═N(C 1~6 alkyl), -NH3, -NH2(C1~6 alkyl), -NH(C 1~6 alkyl)2, and -N(C 1~6 alkyl)3 (wherein any of C1 to C6 may be substituted with -C(O)OH).

[0084] In some embodiments, the organic acid chelator is -C(O)OH, -P(O)(OH), -S(O)-OH, -S(O)OH, -C(=O)OM + , -P(=O)(OH)OM + , -P(=O)(O-)22(M + ), -S(O)2O-M + , -S(O)OM + , -OH, -O(C 1~6 alkyl), ═O, ═NH, ═N(C 1~6 alkyl), -NH3, -NH2(C 1~6 alkyl), -NH(C 1~6 alkyl)2, and -N(C 1~6 alkyl)3 (wherein C 1~6 at least two groups selected from -C(O)OH, -P(O)(OH), -S(O)-OH, -S(O)OH, -C(=O)OM + , -P(=O)(OH)OM + , -P(=O)(O-)22(M + ), -S(O)2O-M + , -S(O)OM + Each M + Li + , Na + , K. + , Cs + , Ag + etc. In some embodiments, at least two heteroatoms (i.e., those with lone pairs of electrons) in the above groups are separated from each other by no more than 2-3 carbons.

[0085] In some embodiments, the organic acid chelator may be an alpha-hydroxy acid or a salt thereof.

[0086] In some embodiments, the organic acid chelator may be a beta-hydroxy acid or a salt thereof.

[0087] In some embodiments, the organic acid chelator may be an α-amino acid or a salt thereof.

[0088] In some embodiments, the organic acid chelator may be a β-amino acid or a salt thereof.

[0089] In many embodiments, the organic acid chelating agent or salt thereof can have a molecular weight of less than about 400 g / mol. For example, the organic acid chelating agent or salt thereof can have a molecular weight of about 400, 375, 350, 325, 300, 275, 250, 225, 200, 175, 150, 125, 100, or 75 g / mol, or within a range between any of the foregoing values, such as between about 75 and about 200, about 150 and 250, etc.

[0090] In some embodiments, the organic acid chelator may be selected from citric acid, tartaric acid, malic acid, oxalic acid, maleic acid, malonic acid, ethylenediaminetetraacetic acid, aspartic acid, glutamic acid, salts thereof, combinations thereof, etc. In some embodiments, the organic acid chelator may be citric acid.

[0091] In some embodiments, the organic acid chelating agent or salt thereof may be present in an amount of about 1% to about 25% by weight based on the weight of the antimicrobial composition. For example, the organic acid chelating agent or salt thereof may be present in an amount of about 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 12, 14, 16, 18, 20, 21, 22, 23, 24, or 25% by weight, or a range between any of the foregoing values, such as about 1 to about 7% by weight, about 3 to about 12% by weight, etc.

[0092] Water-soluble plasticizer In many ways, the plasticizers described herein act in a solubilizing capacity. The plasticizer can facilitate the migration of the organic acid chelating agent or its salt to the water-insoluble polymer. The solubilized organic acid chelating agent becomes available to the surface, for example, the skin surface, when the composition described herein contacts the surface. The organic acid chelating agent can migrate from the water-insoluble polymer to the surface. Without a suitable plasticizer / solubilizer, the organic acid chelating agent remains as an immobilized precipitate, which is hardly available to the surface.

[0093] In some embodiments, the water-soluble plasticizers described herein are not surfactants.

[0094] In some embodiments, the water-soluble plasticizer can have a molecular weight of about 50 g / mol to about 3,000 g / mol, such as about 50, 100, 200, 300, 400, 500, 600, 700, 800, 900, 1,000, 1,200, 1,400, 1,600, 1,800, 2,000, 2,200, 2,400, 2,600, 2,800, or 3,000 g / mol, or a range between any of the foregoing values, such as about 600 to about 1,000 g / mol, about 800 to about 2,200 g / mol, etc.

[0095] In some embodiments, the water-soluble plasticizer may be characterized by a water solubility of greater than 15% w / w, based on the weight of water. The plasticizer may be characterized by a water solubility of greater than 15, 20, 25, 30, 35, 40, 45, 50, 55, 60, 65, 70, 75, 80, 85, 90, 95, or 99% w / w, based on the weight of water, or a value within a range between any of the aforementioned values, e.g., about 70 to about 90% w / w, about 50 to about 80% w / w, etc. In some embodiments, the water-soluble plasticizer may be characterized by a water solubility of greater than 80% w / w. In other embodiments, the water-soluble plasticizer may be 100% w / w soluble in water.

[0096] In some embodiments, the water-soluble plasticizer may be selected from glycerol, polyglycerols having 2 to 20 glycerin units, polyglycerols partially esterified with C1 to C18 alkyl carboxylic acids having at least two free hydroxyl groups (e.g., hexaglycerol monolaurate, decaglycerol monolaurate, polyglyceryl-6 caprate, polyglyceryl-4 oleate, polyglyceryl-10 trilaurate, etc.), polyethylene glycols starting with any of the glycols discussed herein such as polyethylene oxide, polyethylene glycol, polyethylene glycol glyceryl ether, propylene glycol, dipropylene glycol, tripropylene glycol, 2-methyl-1,3-propanediol, sorbitol, dimethyl isosorbide, pentaerythritol, trimethylolpropane, ditrimethylolpropane, random EO / PO copolymers or oligomers, block EO / PO copolymers or oligomers, and combinations thereof.

[0097] In some embodiments, the water-soluble plasticizer may be selected from glycerol, polyglycerol-3, polyglycerol-4, polyglycerol-6, polyglycerol-10, diethylene glycol, polyethylene glycol of an average molecular weight of about 300 to about 800 g / mol, polyethylene glycol-3, polyethylene glycol-6, or a combination thereof.

[0098] In some embodiments, the water-soluble plasticizer may be present in an amount of about 3% to about 35% by weight, based on the weight of the antimicrobial composition. For example, the plasticizer may be present in an amount of about 3, 4, 5, 6, 7, 8, 9, 10, 12, 14, 16, 18, 20, 22, 24, 26, 28, 30, or 35% by weight, or within a range between any of the foregoing values, e.g., about 5 to about 10% by weight, about 20 to about 26% by weight.

[0099] In some embodiments, the water-soluble plasticizer can be characterized by a Log Kow of less than 0.05. For example, the Log Kow of any suitable water-soluble plasticizer can be characterized by a Log Kow of less than about 0.05, 0.02, 0.0, −0.02, 0.05, 0.08, −0.10, −0.20, −0.30, −0.40, −0.50, −0.60, −0.70, −0.80, −0.90, −1.0, −1.2, −1.4, −1.6, −1.8, −2.0, −2.2, −2.4, −2.6, −2.8, or −3.0, or a range between any of the foregoing values, e.g., a Log Kow value of about −1.40 to about −1.80, about −1.0 to about −2.0, etc.

[0100] Chelating Agents and Plasticizers In some embodiments, the water soluble plasticizer may be glycerin and the organic chelating compound may be citric acid or a salt thereof.

[0101] In some embodiments, the water soluble plasticizer may be glycerin and the organic chelating compound may be tartaric acid or a salt thereof.

[0102] In some embodiments, the water-soluble plasticizer may be glycerin and the organic chelating compound may be maleic acid or a salt thereof.

[0103] In some embodiments, the water-soluble plasticizer may be glycerin and the organic chelating compound may be ethylenediaminetetraacetic acid or a salt thereof.

[0104] In some embodiments, the water-soluble plasticizer may be glycerin, the organic chelating compound may be selected from citric acid, tartaric acid, maleic acid, ethylenediaminetetraacetic acid, or salts thereof, and the antimicrobial composition may further include a base buffer, such as NaOH, Na2CO3, NH3, NaClO, Mg(OH)2, NaHCO3, and KH2PO4.

[0105] In some embodiments, the water soluble plasticizer may be polyethylene glycol and the organic acid chelating agent may be citric acid or a salt thereof.

[0106] In some embodiments, the water soluble plasticizer may be polyethylene glycol and the organic acid chelating agent may be tartaric acid or a salt thereof.

[0107] In some embodiments, the water-soluble plasticizer described herein and the organic acid chelating agent or salt thereof described herein may be present in a weight ratio of about 1:1 to about 8:1. For example, the weight ratio may be about 1:1, 1.5:1, 2:1, 2.5:1, 3:1, 3.5:1, 4:1, 4.5:1, 5:1, 5.5:1, 6:1, 6.5:1, 7:1, 7.5:1, or 8:1, or a range between any of the foregoing values, such as about 2:1 to about 4:1, or about 3:1 to about 7:1.

[0108] In some embodiments, the water-soluble plasticizer and the organic acid chelator or salt thereof do not form a covalent complex, for example, a water-soluble plasticizer such as glycerin and an organic acid chelator such as citric acid do not esterify to form glyceryl citrate, so that the acid groups are available to provide antimicrobial properties.

[0109] Photopolymerization initiator In some embodiments, the photoinitiator may be a Norrish Type I photoinitiator. Norrish Type I photoinitiators are cleaved equally into two radical fragments upon irradiation with UV light. These radicals then initiate the polymerization of monomer units. The photoinitiator used herein may be any Norrish Type I photoinitiator known to those skilled in the art.

[0110] Norrish Type II photoinitiators, on the other hand, require a hydrogen donor, such as an amine synergist, to initiate radical formation upon UV irradiation. As shown below, Norrish Type I photoinitiators successfully cure one or more (meth)acrylate monomers, whereas Norrish Type II photoinitiators do not.

[0111] In some embodiments, the photoinitiator may be selected from the Irgacure® or Darocur® group of trade names, such as Irgacure® 651, Irgacure® 819, Irgacure® 184, Irgacure® 2959, or Darocur® 1173. Each of these photoinitiators has a benzoyl fragment that generates a benzyol radical upon irradiation with UV light.

[0112] In some embodiments, the photoinitiator may be 2,2-dimethoxy-2-phenylacetophenone.

[0113] In some embodiments, the photoinitiator may be bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide.

[0114] In some embodiments, the photoinitiator may be 1-hydroxycyclohexyl phenyl ketone.

[0115] In some embodiments, the photoinitiator may be 2-hydroxy-4'-(2-hydroxyethoxy)-2-methylpropiophenone.

[0116] Antibacterial composition - hardened In many embodiments, an antimicrobial composition is described. The antimicrobial composition may include a water-insoluble polymer composition comprising a copolymer derived from a polymerizable mixture comprising at least one high Tg monomer, and optionally a homopolymer thereof, wherein the homopolymer has a Tg of about 40° C. to about 250° C., and at least one low Tg monomer, and optionally a homopolymer thereof, wherein the homopolymer has a Tg of about −70° C. to about 30° C.; an organic acid chelating agent, a salt thereof, or a combination thereof, having a molecular weight of less than about 400 g / mol; and a water-soluble plasticizer capable of solubilizing the organic acid chelating agent or its salt in an amount of at least about 100 g of chelating agent per liter of plasticizer at a temperature of about 20° C. to about 23° C. The antimicrobial composition may be a pressure-sensitive adhesive.

[0117] In many embodiments, the polymerizable mixture may include any combination of monomers described above. In many embodiments, any monomer or combination of monomers may be present in the amounts described above.

[0118] In many embodiments, the organic acid chelating agent may include any of the organic acid chelating agents or salts thereof described above. In many embodiments, the organic acid chelating agent may be present in any of the amounts described above.

[0119] In many embodiments, the water-soluble plasticizer may include any of the water-soluble plasticizers described above. In many embodiments, the water-soluble plasticizer may be present in any of the amounts described above.

[0120] In many embodiments, the (cured) antimicrobial composition may comprise one or more of the additional features described above for the (uncured) antimicrobial composition. The (cured) antimicrobial composition may be prepared from the (uncured) antimicrobial composition described above.

[0121] In some embodiments, the antimicrobial composition may be essentially free of water, ie, less than about 0.1% water by weight.

[0122] Water-insoluble polymer In many embodiments, the water-insoluble polymer composition may be derived from any of the polymerizable mixtures described herein.

[0123] In some embodiments, the water-insoluble polymer may be a random polymer.

[0124] In some embodiments, the water-insoluble polymer may be a block copolymer.

[0125] In some embodiments, the water-insoluble polymers may include random polymers and block copolymers.

[0126] In some embodiments, the water-insoluble polymer may include randomly polymerized portions and block copolymerized portions.

[0127] In some embodiments, the water-insoluble polymer may comprise one or more homopolymers.

[0128] In some embodiments, the water-insoluble polymer can have a Log Kow greater than 0. For example, the water-insoluble polymer can have a Log Kow greater than about 0, 0.2, 0.4, 0.6, 0.8, 1.0, 1.2, 1.4, 1.6, 1.8, 2.0, 2.2, 2.4, 2.6, 2.8, 3.0, 3.2, 3.4, 3.6, 3.8, 4.0, 5.0, 6.0, 7.0, or 8.0, or a value within a range between any of the foregoing values, such as from about 2.0 to about 4.0, from about 2.8 to about 6.0, etc.

[0129] In some embodiments, the water-insoluble polymer may be soluble in water in an amount less than about 15% w / w, based on the weight of the water, for example, less than about 15, 14, 13, 12, 11, 10, 9, 8, 7, 6, 5, 4, 3, 2, or 1% w / w, or within a range between any of the foregoing values, such as about 10 to about 15% w / w, about 5 to about 8% w / w, etc.

[0130] In some embodiments, the water-insoluble polymer may be a polyacid, i.e., derived from monomers having one or more -C(O)OH, -P(O)(OH), -S(O)OH, -S(O)OH, etc.

[0131] In some embodiments, the water-insoluble polymer may be a polyacid consisting essentially of a hydrocarbon backbone and pendant organic acid groups, such as -C(O)OH, -P(O)(OH)-S(O)OH, -S(O)OH, and the like.

[0132] In some embodiments, the water-insoluble polymer may be a polyacid polyester.

[0133] In some embodiments, the water-insoluble polymer comprises a hydrocarbon backbone and pendant organic acid groups, such as —C(O)OH, —P(O)(OH), —S(O)OH, —S(O)OH, and the like, and pendant organic ester groups, such as —C(O)O(C 1~6 It may also be a polyacid polyester consisting essentially of (alkyl).

[0134] antibacterial articles In many embodiments, an antimicrobial article is described. The antimicrobial article can include a substrate having a first surface and a second surface opposite the first surface. The antimicrobial article can include an antimicrobial composition described herein disposed on the first surface.

[0135] In some embodiments, the substrate may be a polymeric film, which may be a woven or nonwoven fabric.

[0136] In some embodiments, the antimicrobial article can further comprise a release liner in contact with the antimicrobial composition.

[0137] In some embodiments, the antimicrobial article can further comprise a delivery liner in contact with the second surface. The delivery liner can cover at least a portion of the second surface and can be removable or permanently adhered to the second surface. The delivery liner can assist a user in applying the substrate to the surface.

[0138] In some embodiments, the antimicrobial composition may be any hardened antimicrobial composition described herein.

[0139] In some embodiments, the antimicrobial article may be in the form of a sheet or roll.

[0140] In some embodiments, the antimicrobial article may be configured in a variety of shapes, including custom shapes to fit over a contoured surface. The antimicrobial article may be in the shape of any wound dressing known in the art.

[0141] In some embodiments, the antimicrobial article is a wound dressing.

[0142] In some embodiments, the antimicrobial article is a surgical drape.

[0143] In some embodiments, the antimicrobial article is an intravenous dressing.

[0144] In some embodiments, the antimicrobial article is a tape or a wrap.

[0145] Method for preparing antibacterial pressure-sensitive adhesives In some embodiments, methods are described for preparing the antimicrobial pressure-sensitive adhesives described herein. The methods may include providing an antimicrobial composition (uncured) described herein and a photoinitiator described herein. The methods may include irradiating the antimicrobial composition and the photoinitiator with electromagnetic radiation at a wavelength of about 280 nm to about 500 nm for a period of time to at least partially cure the antimicrobial composition.

[0146] In many embodiments, the antimicrobial pressure sensitive adhesive may be any of the (cured or partially cured) antimicrobial compositions described herein.

[0147] In some embodiments, the fully cured water-insoluble polymer may contain less than 5% by weight, less than 4% by weight, less than 3% by weight, less than 2% by weight, or less than 1% by weight of unreacted monomer.

[0148] In some embodiments, the partially cured water-insoluble polymer may contain more than 5%, more than 10%, more than 20%, more than 30%, more than 40%, more than 50%, more than 60%, more than 65%, more than 70%, more than 80%, more than 90% by weight of unreacted monomer, hi some embodiments, the partially cured water-insoluble polymer may contain up to about 95% by weight of unreacted monomer.

[0149] In some embodiments, the method may further include contacting the antimicrobial composition with a photoinitiator.

[0150] In some embodiments, the method may further include contacting the substrate with the antimicrobial composition and a photoinitiator prior to irradiating.

[0151] In some embodiments, the radiation may be at a wavelength of about 280, 290, 300, 310, 320, 330, 340, 350, 360, 370, 380, 390, 400, 410, 420, 430, 440, 450, 460, 470, 480, 490, or 500, or within a range between any of the foregoing values, e.g., from about 380 to about 450, from about 300 to about 400, etc.

[0152] In some embodiments, the period can be from about 3 seconds to about 60 minutes. For example, the period can be about 0.05, 0.1, 0.2, 0.3, 0.4, 0.5, 0.6, 0.7, 0.8, 0.9, 1.0, 5.0, 10, 15, 20, 25, 30, 35, 40, 45, 50, 55, or 60 minutes, or a value within a range between any of the foregoing values, such as from about 1.0 to about 5.0 minutes, from about 0.5 to about 40 minutes, etc.

[0153] In some embodiments, the time period may be selected to partially cure the antimicrobial composition. In some embodiments, the partially cured antimicrobial composition may be cured to about 5% to about 70% by weight of monomer. For example, the weight percent of cured monomer in the partially cured water-insoluble polymer mixture may be about 5, 10, 15, 20, 25, 30, 35, 40, 45, 50, 60, 65, or 70 weight percent, or a value within a range between any of the foregoing values, such as about 30 to about 50 weight percent, about 20 to about 40 weight percent, etc.

[0154] In other embodiments, the period of time may be selected to allow the antimicrobial composition to fully cure to provide the antimicrobial pressure sensitive adhesive.

[0155] Method for preparing antibacterial pressure-sensitive adhesives In some embodiments, a method for preparing an antimicrobial pressure-sensitive adhesive is described. The method may include providing an antimicrobial composition described herein and a photoinitiator described herein. The method includes applying a photoinitiator to the antimicrobial composition and the photoinitiator at a power of about 0.01 to about 20 milliwatts per square centimeter (mW / cm). 2), wherein the irradiation is effective to polymerize about 5% to about 70% by weight of the antimicrobial composition to provide a polymer composition. The method may include irradiating the polymer composition with electromagnetic radiation having a wavelength of about 280 to 500 nanometers at an average light intensity of about 20 mW / cm. 2 The method may include irradiating the substrate with electromagnetic radiation having a wavelength of about 280-500 nm at an average light intensity of greater than 1000 nm to provide an antimicrobial pressure sensitive adhesive.

[0156] In some embodiments, the antimicrobial composition may be in a solvent, such as a halogenated organic solvent, e.g., methylene chloride, chloroform, trichloroethylene, an ether organic solvent, e.g., diethyl ether, dimethoxyethane, tetrahydrofuran, a hydrocarbon organic solvent, e.g., pentane, hexane, toluene, benzene, xylene, and other volatile organic solvents, e.g., C 1~6 It may be essentially free of alcohol, ethyl acetate, acetonitrile, and the like.

[0157] In some embodiments, the antimicrobial composition may be partially polymerized prior to irradiation.

[0158] In some embodiments, each radiation may be independently selected from wavelengths of about 280, 290, 300, 310, 320, 330, 340, 350, 360, 370, 380, 390, 400, 410, 420, 430, 440, 450, 460, 470, 480, 490, or 500 nm, or values ​​within ranges between any of the foregoing values, e.g., about 300 to about 380 nm, about 320 to about 440 nm, etc.

[0159] In some embodiments, the antimicrobial composition is irradiated at about 0.01, 0.05, 0.1, 0.2, 0.3, 0.4, 0.5, 1.0, 2.0, 4.0, 6.0, 8.0, 10.0, 12.0, 14.0, 16.0, 18.0, or 20.0 mW / cm 2 or a value within a range between any of the aforementioned values, e.g., from about 0.1 to about 2.0 mW / cm 2 , about 6.0~about 12.0mW / cm 2The average light intensity may be any one of the aforementioned wavelength values.

[0160] In some embodiments, the irradiation is effective to polymerize about 5, 10, 15, 20, 25, 30, 35, 40, 45, 50, 55, 60, 65, or 70 wt. % of the antimicrobial composition, or a value within a range between any of the foregoing values, such as about 25 to about 30 wt. %, about 10 to about 50 wt. %.

[0161] In some embodiments, the irradiation of the polymerizable composition is at about 20, 19, 18, 17, 16, 15, 14, 13, 12, 11, 10, 9, 8, 7, 6, 5, 4, 3, 2, 1, 0.05, 0.02, or 0.01 mW / cm 2 or less, or a value within a range between any of the aforementioned values, e.g., about 1 to about 7 mW / cm 2 , about 10~15mW / cm 2 The average light intensity may be any one of the aforementioned wavelength values.

[0162] Methods for disrupting biofilms In some embodiments, methods are described for preventing or disrupting biofilm on a surface. The methods may include providing an antimicrobial article described herein and contacting the antimicrobial article with the surface for a period of time, wherein the contact is effective to prevent the formation or growth of biofilm or disrupt an existing biofilm on the surface.

[0163] In other embodiments, the method may include providing an antimicrobial composition described herein in place of the antimicrobial article and contacting the antimicrobial composition (when hardened) with the surface for a period of time.

[0164] In some embodiments, the surface is skin or tissue. In some embodiments, the skin or tissue is mammalian skin or tissue. In some embodiments, the skin or tissue has a wound or other injury. In some embodiments, the tissue may be selected from mucosal tissue, a chronic wound, an acute wound, a burn, or the like.

[0165] In other embodiments, the surface is a medical surface, such as a surgical device (e.g., scalpel, scissors, blade, forceps, drape, etc.), a medical device (e.g., catheter, stent, artificial joint, dental implant, etc.), floor tile, countertop, tub, dish, glove, swab, cloth, sponge, foam, nonwoven, and paper product.

[0166] In some embodiments, the antimicrobial article (or antimicrobial composition) may be effective in disrupting biofilms of various microbial species, such as gram-positive bacteria, gram-negative bacteria, fungi, protozoa, mycoplasma, yeast viruses, lipid-enveloped viruses, etc. For example, the antimicrobial composition or an article made therefrom may reduce the numbers of Staphylococcus spp., Streptococcus spp., Pseudomonas spp., Enterococcus spp., Escherichia spp., Aspergillus spp., Fusarium spp., Candida spp., etc. For example, the antimicrobial composition or an article made therefrom may be effective against Staphylococcus aureus, methicillin-resistant Staphylococcus aureus (MRSA), Staphylococcus epidermidis, Streptococcus pneumoniae, Enterococcus faecalis, vancomycin-resistant Enterococcus (VRE), Pseudomonas aeruginosa, Escherichia coli, Aspergillus niger, Aspergillus fumigatus, Aspergillus clavatus, Fusarium solani, and the like. solani, Fusarium oxysporum, Fusarium chlamydosporum, Candida albicans, Candida glabrata, Candida krusei, and the like.

[0167] In some embodiments, the antimicrobial article (or antimicrobial composition) may be contacted with the surface for a period of about 30, 60, 90, 120, 150, 180, or 210 minutes, or a value within a range between any of the foregoing values, e.g., about 30 to about 120 minutes, about 90 to about 180 minutes, etc. In other embodiments, the antimicrobial article may be contacted with the surface for a period of more than about 1, 2, 3, 4, 5, 12, or 24 hours, or a value within a range between any of the foregoing values, e.g., about 2 to about 5 hours, about 12 to about 24 hours, etc. In some embodiments, the antimicrobial article may be contacted with the surface for a period of about 1, 2, 3, 4, 5, 6, or 7 days, or a value within a range between any of the foregoing values, e.g., about 1 to about 2 days, about 2 to about 5 days, etc.

[0168] Methods for reducing microorganisms In some embodiments, a method for reducing the number of microorganisms on a surface is described. The method may include providing an antimicrobial article as described herein and contacting the antimicrobial article with the surface for a period of time, wherein the contact is effective to reduce the number of microorganisms in the area of ​​the surface contacted by the antimicrobial article.

[0169] In other embodiments, the method may include providing an antimicrobial composition described herein in place of the antimicrobial article and contacting the antimicrobial composition with the surface for a period of time.

[0170] In some embodiments, the antimicrobial article (or antimicrobial composition) may be effective in reducing the number of various microorganisms described herein.

[0171] In some embodiments, the surface may be any skin surface, an instrument surface, a surface prepared for holding an instrument, or any other surface requiring disinfection, such as other surfaces described herein.

[0172] In some embodiments, the antimicrobial article (or antimicrobial composition) may be contacted with the surface for a period of about 30, 60, 90, 120, 150, 180, or 210 minutes, or a value within a range between any of the foregoing values, e.g., about 30 to about 120 minutes, about 90 to about 180 minutes, etc. In other embodiments, the antimicrobial article may be contacted with the surface for a period of more than about 1, 2, 3, 4, 5, 12, or 24 hours, or a value within a range between any of the foregoing values, e.g., about 2 to about 5 hours, about 12 to about 24 hours, etc. In some embodiments, the antimicrobial article may be contacted with the surface for a period of about 1, 2, 3, 4, 5, 6, or 7 days, or a value within a range between any of the foregoing values, e.g., about 1 to about 2 days, about 2 to about 5 days, etc.

[0173] Methods for treating infectious diseases In some embodiments, methods for treating or preventing an infection are described. The methods may include providing an antimicrobial article described herein and contacting the antimicrobial article with a surface in need of disinfection for a period of time, wherein the contacting is effective to ameliorate one or more symptoms of the infection, and wherein the contacting is effective to prevent the onset of an infection characterized by one or more symptoms of the infection.

[0174] In some embodiments, symptoms of an infection may include, for example, redness, swelling, inflammation, elevated local or body temperature, the presence of pus, combinations thereof, and the like.

[0175] kit In many embodiments, kits are described that may include any of the antimicrobial articles described herein and a set of instructions directing a user to perform the method steps described herein for reducing the number of microorganisms on a surface or the method steps described herein for disrupting a biofilm on a surface. [Example]

[0176] The objects and advantages of the present disclosure are further illustrated by the following examples, but the particular materials and amounts thereof recited in these examples, as well as other conditions and details, should not be construed to unduly limit the disclosure. These examples are for illustrative purposes only and are not intended to limit the scope of the appended claims. [Table 1]

[0177] Mixture A: Procedure for dissolving citric acid in glycerol 15 grams (g) of citric acid was added to a 240 mL glass jar containing 100 g of glycerol at room temperature. The jar was sealed and placed on a rotating mixer for 60-70 hours until a clear solution was obtained. This solution is referred to as Mixture A.

[0178] Mixture B: Mixing citric acid and sodium hydroxide in glycerol To a 240 mL glass jar, 26.5 g of citric acid, 3.5 g of sodium hydroxide, and 70 g of glycerol were added at room temperature. The jar was sealed and placed on a rotating mixer for 60-70 hours until a clear solution was obtained. This solution is referred to as Mixture B.

[0179] Procedure for Making Pressure Sensitive Adhesives Mixture C (containing no organic acid chelating agents or glycerol) A pressure-sensitive adhesive precursor composition was prepared by combining 95 g of IOA, 5 g of AA, and 0.05 g of IRGACURE 651. This composition was partially polymerized under a nitrogen atmosphere by exposure to low-intensity (UV-A) ultraviolet light to yield a cloudy, coatable, viscous syrup. A rectangle approximately 100 mm x 150 mm and 1-3 mm deep was created by placing 3M VHB™ tape onto a release liner. The cloudy syrup was poured into this rectangular mold, covered with an additional sheet of release liner, and placed under a rapid-start bulb under a nitrogen atmosphere for 30 minutes to 1 hour. The resulting cured adhesive was further tested for zone of inhibition and quantitative tack using a tack tester.

[0180] Mixture D (containing no organic acid chelating agents or glycerol) A pressure-sensitive adhesive precursor composition was prepared by combining 99 g of IOA, 1 g of AA, and 0.05 g of IRGACURE 651. This composition was partially polymerized under a nitrogen atmosphere by exposure to low-intensity (UV-A) ultraviolet light to yield a cloudy, coatable, viscous syrup. A rectangle approximately 100 mm x 150 mm and 1-3 mm deep was created by placing 3M VHB™ tape onto a release liner. The cloudy syrup was poured into this rectangular mold, covered with an additional sheet of release liner, and placed under a rapid-start bulb under a nitrogen atmosphere for 30 minutes to 1 hour. The resulting cured adhesive was further tested for zone of inhibition and quantitative tack using a tack tester.

[0181] Example 1 A pressure-sensitive adhesive precursor composition was prepared by combining 80 g of IOA, 20 g of AA, 0.05 g of IRGACURE 651, and 11.5 g of Mixture A. This composition was partially polymerized under a nitrogen atmosphere by exposure to low-intensity (UV-A) ultraviolet light to yield a cloudy, coatable, viscous syrup. The syrup was observed over the next three days and showed no settling or separation.

[0182] A rectangle approximately 100 mm x 150 mm and 1-3 mm deep was created by placing 3M VHB™ tape onto a release liner. The cloudy syrup was poured into this rectangular mold, covered with an additional sheet of release liner, and placed under a rapid-start bulb under a nitrogen atmosphere for 30 minutes to 1 hour. The resulting cured adhesive was further tested for zone of inhibition and quantitative tack using a tack tester.

[0183] Example 2 A pressure-sensitive adhesive precursor composition was prepared by combining 80 g of IOA, 20 g of AA, 0.05 g of IRGACURE 651, and 2 g of citric acid. The syrup was partially polymerized under a nitrogen atmosphere by exposure to low-intensity (UV-A) ultraviolet light. The resulting partially cured syrup contained precipitated citric acid particles.

[0184] Example 3 A pressure sensitive adhesive precursor composition was prepared by combining 90 g of the already partially polymerized Mixture C syrup with 10 g of Mixture B and mixing on a roller overnight.

[0185] A rectangle approximately 100 mm x 150 mm in size and 1-3 mm deep was created by placing 3M VHB™ tape onto a release liner. The cloudy syrup was poured into this rectangular mold, covered with an additional sheet of release liner, and placed under a rapid-start bulb in a nitrogen atmosphere for 30 minutes to 1 hour. The resulting adhesive was tacky to the touch.

[0186] Example 4 A pressure-sensitive adhesive precursor composition was prepared by combining 80 g of the already partially polymerized Mixture C syrup with 20 g of Mixture B and mixing overnight on a roller. A rectangle approximately 100 mm x 150 mm and 1-3 mm deep was created by placing 3M VHB™ tape onto a release liner. The cloudy syrup was poured into this rectangular mold, covered with an additional sheet of release liner, and placed under a rapid-start bulb in a nitrogen atmosphere for 30 minutes to 1 hour. The resulting cured adhesive was further tested for inhibition zone and quantitative tack using a tack tester.

[0187] Example 5 A pressure-sensitive adhesive precursor composition was prepared by combining 65 g of the already partially polymerized Mixture C syrup with 35 g of Mixture B and mixing overnight on a roller. A rectangle approximately 100 mm x 150 mm and 1-3 mm deep was created by placing 3M VHB™ tape onto a release liner. The cloudy adhesive mixture was poured into this rectangular mold, covered with an additional sheet of release liner, and placed under a rapid-start bulb in a nitrogen atmosphere for 30 minutes to 1 hour. The resulting cured adhesive was further tested for inhibition zone and quantitative tack using a tack tester.

[0188] Example 6 A pressure-sensitive adhesive precursor composition was prepared by combining 90 g of the already partially polymerized Mixture D syrup with 10 g of Mixture B and mixing overnight on a roller. A rectangle approximately 100 mm x 150 mm in dimensions and 1-3 mm deep was created by placing 3M VHB™ tape onto a release liner. The cloudy adhesive mixture was poured into this rectangular mold, covered with an additional sheet of release liner, and placed under a rapid-start bulb in a nitrogen atmosphere for 30 minutes to 1 hour. The resulting cured adhesive was further tested for inhibition zone and quantitative tack using a tack tester.

[0189] Antibacterial testing using zone of inhibition The zone of inhibition test, also known as the Kirby-Bauer test, is a qualitative method for measuring antimicrobial resistance. The zone of inhibition test was performed using the cured adhesive of Example 1. A P. aeruginosa culture was streaked onto tryptic soy agar and incubated overnight at 35°C. A bacterial suspension was prepared in phosphate-buffered water (PBW) to a density of approximately 8 logs using a McFarland turbidity standard 0.5 and further diluted 1:1000 in PBW. The diluted suspension was streaked onto the surface of Mueller-Hinton agar and allowed to dry to form a lawn. A sample of the cured adhesive of Example 1 was placed on the surface of the agar, and the plate was placed in an incubator at 35°C overnight. The plate was then inspected, and a zone of inhibition was observed, indicating that P. aeruginosa was susceptible to the cured adhesive. Values ​​are reported in Table 1 in "mm" as the circular zone formed around the sample. For example, a value of 6 mm represents a distance of 6 mm from the edge of the circular sample.

[0190] Adhesion test Adhesion testing was performed using a TA-XT2 Texture Analyzer. Glass microslides (VWR catalog number 48312-002) were used to attach double-sided adhesive tape (3M Medical Tape 1577, Double Sided Differential Adhesive Polyester, 60# Liner, Configurable, Synthetic Rubber Adhesive / Tackified Acrylic Adhesive) to which adhesive was applied. The force was 10.0 g, the distance was 10 mm, and the test speed was 2 mm / sec. The work of adhesion was recorded and is listed in Table 1. [Table 2]

[0191] Example 1 provided the highest adhesion and desirable inhibition. Although a significant loss of adhesion (Example 5) was observed with higher amounts of glycerol and citric acid, higher amounts of glycerol and citric acid provided the highest antimicrobial properties. equivalent

[0192] Those skilled in the art will recognize, or be able to ascertain using no more than routine experimentation, many equivalents to the specific embodiments specifically described herein which equivalents are intended to be encompassed by the following claims.

Claims

1. An antibacterial composition comprising: at least one high Tg monomer having a Tg of about 40°C to about 250°C, and optionally its homopolymer, and at least one low Tg monomer having a Tg of about -70°C to about 30°C, and optionally its homopolymer in a polymerizable mixture, wherein after polymerization, the polymerizable mixture forms a water-insoluble polymer composition comprising a copolymer derived from the at least one high Tg monomer and the at least one low Tg monomer; a polymerizable mixture, an organic acid chelating agent having a molecular weight of less than about 400 g / mol, its salt, or a combination thereof, a water-soluble plasticizer capable of solubilizing the organic acid chelating agent or its salt in an amount of at least about 100 g of the chelating agent per liter of the plasticizer at a temperature of about 20°C to about 23°C, An antibacterial composition comprising.

2. An antibacterial composition comprising: at least one high Tg monomer having a Tg of about 40°C to about 250°C, and optionally its homopolymer, and at least one low Tg monomer having a Tg of about -70°C to about 30°C, and optionally its homopolymer a water-insoluble polymer composition comprising a copolymer derived from a polymerizable mixture; an organic acid chelating agent having a molecular weight of less than about 400 g / mol, its salt, or a combination thereof, a water-soluble plasticizer capable of solubilizing the organic acid chelating agent or its salt in an amount of at least about 100 g of the chelating agent per liter of the plasticizer at a temperature of about 20°C to about 23°C, An antibacterial composition, which is a pressure-sensitive adhesive, comprising.

3. The antibacterial composition according to claim 1 or 2, wherein the at least one high Tg monomer is represented by formula (I): 【Chemical 1】 [wherein, X is -C(O)OR ４ａ , -C(O)N(R ５ａ )(R ５ａ ), -CN, -N(R ５ａ )-C(O)-R ６ａ selected from R １ａ is independently selected from -H, C alkyl optionally substituted with one or more -OH １～６ -(CH ２ ) ｎ -C(O)-R ７ａ and R ２ａ is independently selected from -H, C optionally substituted with one or more -OH １～６ alkyl, or R ２ａ and R ４ａ or R ２ａ and R ５ａ together with the atoms to which they are attached form a 5- to 6-membered heterocycle, R ３ａ is independently selected from -H, -OH, or C optionally substituted with one or more -OH １～６ alkyl R ４ａ is -H, C １～６ alkyl, or C optionally substituted with one or more C １～４ cycloalkyl optionally substituted with alkyl ４～８ and is Each R ５ａ is independently C １～６ alkyl which may be substituted with -H or one or more -OH R ６ａ is -H, or C １～６ is alkyl, or R ５ａ and R ６ａ together with the atoms to which they are attached form a 4- to 7-membered heterocyclic ring, R ７ａ is -OR ８ａ or -N(R ８ａ )(R ８ａ ) or R ７ａ and R ４ａ or R ７ａ and R ５ａ together with the atoms to which they are attached form a 5- or 6-membered heterocycle, Each R ８ is independently selected from -H and C １～６ alkyl, n is an integer in the range of 1 to 6] represented by.

4. The antibacterial composition according to any one of claims 1 to 3, wherein the at least one low Tg monomer is represented by formula (II): 【Chemical 2】 [wherein, Y is -C(O)O-R ４ｂ or -OC(O)-(C １～６ alkyl), R １ｂ is independently selected from -H or C １～１８ alkyl, R ２ｂ is independently selected from -H or C １～１８ alkyl, R ３ｂ is independently selected from -H or C １～１８ alkyl, R ４ｂ is independently selected from -H, or C optionally substituted with one or more -OH and -CN １～１８ alkyl R １ , R ２ , R ３ , or R ４ wherein at least one of is C ４～１８ alkyl] represented by.

5. The antibacterial composition according to any one of claims 1 to 4, characterized by one or more of: the at least one high Tg monomer is present in an amount of about 1 part by weight to about 50 parts by weight of the polymerizable mixture, and the at least one low Tg monomer is present in an amount of about 50 parts by weight to about 99 parts by weight of the polymerizable mixture represented by.

6. The antibacterial composition according to any one of claims 1 to 5, wherein the polymerizable mixture contains isooctyl acrylate, 4-hydroxybutyl acrylate, acrylic acid, or a combination thereof.

7. The polymerizable mixture further contains at least one medium Tg monomer having a Tg of about -20°C to about 70°C for its homopolymer, and optionally its homopolymer, The antibacterial composition according to any one of claims 1 to 6, wherein the at least one medium Tg monomer is present in an amount of about 5 parts by weight to about 50 parts by weight of the polymerizable mixture.

8. The antibacterial composition according to claim 7, wherein the polymerizable mixture contains isooctyl acrylate, 4-hydroxybutyl acrylate, acrylic acid, and hydroxyethyl acrylate.

9. The organic acid chelating agent, its salt, or a combination thereof is present in an amount of about 1% to about 25% by weight based on the weight of the antibacterial composition, and is selected from citric acid, sodium citrate, tartaric acid, malic acid, ethylenediaminetetraacetic acid, their salts, and combinations thereof. The antibacterial composition according to any one of claims 1 to 8.

10. The water-soluble plasticizer is present in an amount of about 3% to about 25% by weight based on the weight of the antibacterial composition, and is selected from glycerol, polyglycerol-3, polyglycerol-4, polyglycerol-6, polyglycerol-10, diethylene glycol, polyethylene glycol with an average molecular weight of about 300 to about 800, and combinations thereof. The antibacterial composition according to any one of claims 1 to 9.

11. An antibacterial article, a substrate having a first surface and a second surface opposite to the first surface, and the antibacterial composition according to any one of claims 2 to 10 disposed on the first surface An antibacterial article comprising.

12. A method for preparing an antibacterial pressure-sensitive adhesive, providing the antibacterial composition according to any one of claims 1 to 10, combining the antibacterial composition with a photoinitiator, The antibacterial composition and the photoinitiator are irradiated with electromagnetic radiation having a wavelength of about 280 to 500 nanometers at an average light intensity of about 0.01 to about 20 milliwatts per square centimeter (mW / cm ２ ), wherein the irradiation is effective to polymerize about 5 wt% to about 70 wt% of the monomer to provide a polymer composition, and Irradiate the polymer composition with electromagnetic radiation having a wavelength of about 280 to 500 nm at an average light intensity of more than about 20 mW / cm ２ to provide the antibacterial pressure-sensitive adhesive. A method comprising.

13. Reducing the number of microorganisms on a surface, preventing the formation or growth of biofilms on a surface, and destroying the biofilms on the surface A method for one or more of the above, providing the antibacterial article according to claim 11, contacting the antibacterial article with the surface for a certain period of time comprising, wherein said contact reduces the number of said microorganisms on said surface, prevents the formation or growth of biofilm on said surface, and destroys existing biofilm on said surface is effective for one or more of the foregoing, a method. **Claim 14**: The antimicrobial article according to claim 11 for use in the manufacture of a medicament for treating or preventing an infectious disease. **Claim 15** A kit comprising: the antimicrobial article according to claim 11; and a set of instructions for instructing a user to contact the antimicrobial article with a surface. A kit comprising the foregoing.

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